Scott Sheridan is a seasoned entrepreneur and trader who co-founded thinkorswim, a transformative platform later acquired by TD Ameritrade. We spoke about his journey from trading on the Chicago Board Options Exchange to building and selling multiple businesses, the mindset required to navigate entrepreneurial risks, and the importance of giving back to the community. Sheridan’s story is a masterclass in resilience, adaptability, and strategic thinking, offering practical wisdom for aspiring entrepreneurs.

The conversation highlights Sheridan’s philosophy of “eating what you kill,” a trader’s mentality that shaped his entrepreneurial approach. He emphasizes the need for minimal personal expenses to preserve capital for business growth, recalling, “When my partner and I started thinkorswim, we took a minimal, minimal salary and we never changed it.” This discipline underscores a key takeaway: prioritizing the business over personal gain is critical in the early stages.

Sheridan’s insights on pivoting are particularly compelling. He warns against rigidity, noting, “Most people become too rigid and they’re not willing to modify. They say, this is my idea. I’m not pivoting from that idea. And typically, that leads to problems, which leads to failure.” Instead, he advocates for launching a minimum viable product (MVP) and iterating based on feedback, a strategy that avoids “paralysis by analysis.” As he puts it, “Get the idea out there as quickly as you could possibly get the idea out… it puts pressure on the dev team to build as quickly and iterate as fast as they can.”

Another standout topic is the power of partnerships and trust. Sheridan’s 36-year collaboration with his business partner exemplifies the value of complementary strengths and mutual confidence. “I would hand him my checkbook, I would hand him my credit cards. Wouldn’t even think about it,” he says, highlighting the rarity and necessity of such trust. This reinforces a key lesson: success is a team effort, not a solo endeavor.

Sheridan’s reflections on giving back add depth to his story. His support for Lurie’s Children’s Hospital and Cooper Union, where his father studied, reveals a commitment to social responsibility. The emotional impact of receiving letters from students who benefited from his fund is palpable: “I had tears in my eyes because… they couldn’t have come to this school without your help.” This underscores a profound takeaway: true success extends beyond financial gain to creating lasting impact.

From Sheridan’s candid admission that he didn’t have a paycheck until age 35 to his view of business as a game akin to trading, the episode is packed with gritty, actionable advice. His father’s influence, a lifelong entrepreneur who worked until 36 hours before his passing, adds a personal layer, reminding us that passion drives persistence. As Sheridan notes, “It’s not work if you’re excited to go do it.”

Key Takeaways:

Embrace adaptability: Be open to modifying your idea based on market feedback to avoid failure.
Launch fast, iterate faster: Release an MVP to validate concepts and refine based on real-world input.
Build trusted teams: Surround yourself with reliable, complementary partners to amplify success.
Plan for a longer runway: Anticipate that time and costs will likely double or triple initial estimates.
Give back meaningfully: Success carries a responsibility to support your community, whether through time or resources.

Sheridan’s journey is a testament to the grind and glory of entrepreneurship, proving that with risk, resilience, and a willingness to pivot, ideas can indeed come to fruition.

S5E03 - Write Me A Letter